The Dealbreaker
by socatherine
Summary: Post season 4 lit, with Jess angst and Rory inner turmoil.
1. Dodger, forever and always

Set somewhere during season 5, when we don't get to know anything about the one and only Jess. This is just musings in my head after watching Let Me Hear Your Balalaikas Ring Out and seeing him so grown-up made me wonder where he got his drive to write _The Subsect._ This is short, I know, but I hope this makes someone just a tiny bit happy...

-C

* * *

Jess Mariano could not get her off his mind. Again.

He was sitting in a hole-in-the-wall coffee shop in Philadelphia he had found a few months ago after his move out to Pennsylvania, trying yet again to see what she saw in _We The Living_. He told himself he walked in the first time because he liked coffee, but the real reason was because the menu was hand-written on special boards, and it reminded him of…the only place that he ever found what a home should have: love. _I've got to call Luke,_ he thought._ I need to apologize for all the shit I put him through. _

He drummed his fingers on table and sighed. It had been three years since he moved to Stars Hollow. Three years since he met her. The Girl, Matt and Chris called her. The one that inspired Jess Mariano to be great. That had been their little joke, but they didn't realize how much it hurt Jess to hear about it. About her. He had grown up a lot in three years, even he would admit. He got his GED, moved away from New York, and Matt and Chris had convinced him to take a few night courses at a community college close to their apartment. He could imagine how proud she would be if she knew. How proud she would've been two years ago if he'd done what he was supposed to. Why did he have to be so stubborn? Why couldn't he have just listened to her and Luke? She would sill be with him, instead of with Dean (God, he prayed that she wasn't...) or some rich Yale kid. The thought made him cringe. Yale...he hated Yale.

It had been a year since the horrible meeting at Yale in which everything had gone wrong, but he still thought of her every day of his life. Her hair, her face, her hips. God, her eyes! He missed those eyes…

He let out a snort. If Matt or Chris found out the whole story about Rory, he would never, _ever_, live it down. _Sap!_ they'd call him, which was probably true. He was still whipped for her, and he hadn't seen her in more than a year! Was he insane? _Probably,_ he thought.

He got up, threw a 5 on the table, and walked out into the pouring rain. A group of college girls were under umbrellas laughing and screeching about getting wet. One of them caught Jess' eye and smiled. He grimaced in response. _I need to be nicer_, he thought to himself. _No one likes an angry moron._ _Well, one person did. And I blew it. _

When he had come to Yale, he was so sure that he would run away with him, but she was way angrier that Jess had figured she would be. What did that mean? Did she hate him? It sure seemed like she did. But a smaller part of Jess' capable brain told him that it was because she loved him back, and he had broken her heart when he'd left to chase his bum of a father to California. _Rory, I ran away to face my problems head on! Not because I didn't like you or you made me angry! I love you, Rory. I love you_…

He had actually said those three words only once in his life and it was at a horrible time. Probably the worst timing imaginable. But that's what you get with Jess Mariano: bad timing and broken promises.

He was such a failure. A pathetic failure to everyone who even remotely loved him: Luke, Liz, and most of all Rory.

By the time he made it back to the tiny apartment he shared with Matt and Chris, he was soaked and in an awful mood.

He had changed for her. He had made himself a better person just for her. _And here's the dealbreaker, idiot. She doesn't even care._

Was it possible that Jess Mariano loved a girl more than the girl liked him? He didn't know. It had never happened before. He was always the one that broke up with girls. Not to mention, none of those girls knew Dickens. He smiled slightly, throwing that horrid Ayn Rand he was (unsuccessfully) reading earlier on his bed. She had let him borrow that one before he ran from Stars Hollow.

He decided that things needed to change. Now.

He pulled out that old notebook he'd been meaning to use, and wrote down every mindless thought he had in his mind. _Maybe there's something worthwhile in there. Maybe this is my saving grace, like Rory said years ago. _

"You've got a great brain, Jess."

Well, if she said it, it must be true. So he would sure as hell use his brain to win her back.

He had to win her back.


	2. I couldn't have done it without you

It was strange timing, even Rory Gilmore would admit. With everything that had happened, all the pure _chaos_ that was the last few months, the one person that Rory had found utterly constant (in a bad way albeit) had_ changed._ He looked like an angel compared to the things she had done recently. She still couldn't believe she had stolen a yacht. She, Rory, had stolen something! To make it even worse, a big something! And all those "sleepovers" at Paris's. She laughed out loud now, finding it hard to believe that her grandmother had eaten those lies up.

When Jess had shown up at her grandparents' place (with no black eye this time), she had been shocked. After their last meeting, she didn't think they would ever see each other again. She had been very, very tough on him, even though they both knew he deserved it. Then, he looked, well, the only word that her vocabulary that could describe him best was brokenhearted. She winced at that thought. Now, however, he looked _good._ Sturdy and lean, but grown up, in a way she would have only believed with her own two eyes. He still had the crazy hair-do, but it was tamed into a beautiful mess on top of his head, and had stuble on his face, as if he hadn't slept in days. And he wrote a _book._ _He_ wrote a _book._ A great book, in fact. A book that she would recommend to anyone. However "happy" she was with Logan, she really cared for Jess Mariano.

_Don't kid yourself. You love him. Still, _she thought to herself. And it was true. If he had stuck around for one more minute, he would have heard her say "I love you, too." She had, to an empty Stars Hollow, after watching his car speed away.

Now, as she speeds down the highway to Yale to start her classes again, she realizes how stupid she really was. Dropping out of _Yale_? And started living with her _grandparents?_ In the room that her grandmother decorated with a 98 degrees poster and Hello Kitty! Stuff sophomore year in high school! Who sucked her mind and possessed her body?

_Logan_, her competent brain told her. _He_ was the one who wanted to party, to steal things, to be basically bipolar about everything. And she knew that their relationship was still "open," no matter how much she wanted it to be as closed as any Hemingway book.

She smiled at her lame joke, with Jess' words said so long ago ringing in her ears: "You know, ___Earnest has only lovely things to say about you_."

She found it ironic that he was the one who snapped her out of it. Who, in about a one minute conversation in which _he_ did most of the talking—yelling, actually—told her everything she already knew, but didn't have the guts to admit. And he remembered her _birthday!_

Once again, Rory had the feeling that if he had stuck around for five more minutes, she would probably be crying into his chest and blubbering her love.

In her head, she wished he would have stayed. But that was in her head. In real life…it would have made things much more complicated.

She felt stupid for not figuring this out until now, but her relationship with Logan was simple, easy. It was routine. She liked routine. Right? All the lists, all the school, living in Stars Hollow. Even Dean, for God's sake, was a routine.

Her relationship with Jess, however, was anything but simple. Jess had never been good at communicating what he actually needed to say. He should have asked for help with school, but he was too proud. He should have told her he was living, but he was too much of a wimp.

_Don't try to push all the blame on him, Rory, _she frustratingly told herself. She wasn't the best girlfriend in the world. She pushed him around, acted like she owned him, and always compared everything he did to Dean. There were some good parts of the relationship (he could always make her spine tingle), but they were both just too immature for the intellectual level they were both on.

Jess' words two years ago spun in her head: "You know we're supposed to be together. I knew it the first time I saw it two years ago, and you know it too." Maybe he was right. Maybe they were supposed to be together. But their timing was always off.

Rory knew one thing for certain: she missed him. She missed his eyes, and his smirk, and his annoyingly gorgeous hair. She missed his mannerisms, and the crook in his neck she fit into just right (because, let's face it, he's short). She missed their banter, and their sarcasm, and the...love he had for her. She couldn't believe she didn't see it in high school.

Once again, Jess Mariano made Rory question herself.

But what was she possibly supposed to do? She was in love with Logan. She was sure of it…wasn't she? He was everything she always wanted: adventurous, smart, affectionate, and could give her everything she would ever think to want.

But did she want _him?_ That was the question that was impossible to answer.


	3. Maybe we'll catch up a better time

A/N: Don't hate me! I had to do it, no matter how depressed it made me. But there are bigger and better things planned for this, don't worry. Much bigger and much better.

Also, I just realized that Logan's last name is a brand of ketchup. Just sayin'.

Andddd, background music for this chapter is .com/watch?v=LEt1xwwcqoU. I always have thought it fits perfectly with Rory and Jess' relationship.

He was shaking. This could not have just happened.

She picked Blond Dick at Yale over him.

She _kissed _him and _still_ picked Ketchup Boy.

She had come _all the way _to Truncheon to break his heart again. And she had known exactly what she had come for. _Did she really think she was going to sleep with me to get back at that cheater? And did I really tell her that she could tell him that we did? Was I on drugs? _

The truth was he had wanted to do it. He had lived like a eunuch since he was seventeen waiting for her. He wanted to make his fantasies come to life, but of course his fantasies never come true. Since when could he even hope he was that lucky? _Never,_ he thought.

He wrote her a _book._ _He _wrote_ her_ a _book_! Did she still not care that he got his life together for her? All for her, for no one else, not even himself. He didn't care about himself. It was all for her.

His heart shattered into about a million pieces, and he absentmindedly thought it was ironic that she had meant to hurt Logan, but ended up injuring him instead. That was all his life was, irony.

He grabbed a beer out of the fridge and chugged. He needed to get _drunk._ Maybe he would forget that this amazingly horrific day ever happened. Halfway through the bottle of Bud Light, though, he started to cry. He wasn't even intoxicated, he was in the middle of broad daylight, and he was _crying._ It was really pathetic how much of a hold Rory Gilmore had on his heart. He didn't think that she realized how truly killed he would be because of this. Maybe she didn't care.

He should have been able to let her go, he should be able to get over her, especially after this fiasco, but he knew without a doubt that there was still a huge part of his soul that loved her more than anything else in the world.

_These are the times that I wish I didn't give up smoking, _he thought wryly. He had really changed. If she had given him the time to explain, he could have told her about the GED, about the college classes, about even the reviews from the Philadelphia Inquirer and Pittsburgh Post Gazette about his book. Despite the downplaying of his novella, he was really proud of it.

He didn't get it: what could possibly make Blond Dick better than he? He wasn't the greatest guy ever, but at least he didn't drive a Porche. What a jerk. He never remembered Rory being the superficial type. Maybe he didn't know Rory at all.

_That's not it, _he told himself. _You know her better than anyone. _He thought back to the last time they had seen each other, when he practically screamed the truth at her. She obviously needed to hear it, judging from the way she acted, the way she held herself up, like she was afraid to let go for fear of spontaneous combustion. He remembered how her face had gone into total surprise when he mentioned her birthday. What happened to make that memorable? Did Dickhead forget it or something?

He was an emotional wreck.

He shook his head, and downed his third beer. Things were getting fuzzy. He had imagined what it would be like to see Rory Gilmore again, but the one thing he knew for sure was that things were not supposed to go like this. _"Maybe we'll catch up at a better time."_ What is a better time? And why was their timing always shit? Why couldn't he get this one thing that he wanted? Did life have to hate him this much?

There was nothing left to do when it came to Rory Gilmore; he had exhausted all of his opportunities. Either she had to come to him, or there would be no them. And he wanted a 'them' really, _really _bad.

As for now, he would wallow with some Ben and Jerry's chunky monkey, that bottle of vodka he forgot he had, and _Almost Famous. _

He snorted. Lorelai herself would be proud.


	4. The Dreams of a Monosyllabic

Sorry for the wait guys, I've been really completely busy with school and band, but it's fall break, and I got a muse (ahem, season 3), so the first part to the two-part finale is finally here! Now, since Jess doesn't show up after season 6, this is future lit, but who doesn't like anything lit?

Also, I really hope they make a movie…Just saying. And Jess needs to be in it. Enjoy, and please Review.

-socatherine

It came in the mail on a day in May, but he couldn't tell you which one. It was a small envelope, just big enough to fit a letter, and there was no return address. He was on the phone when he opened it, and seeing her handwriting made him alternately cringe and shake, since she had made no contact with him since that horrible day at Truncheon the year before. It was short and sweet and to the point (just like Rory) and it said:

_Dear Jess,  
I've really made some big mistakes in my life, and you were the only person that got to me. That has to mean something, right? Please come to my graduation, so we can catch up.  
Rory_

Attached with it was a Yale University ticket, and in the twenty seconds it took to read the note, he became furious. He turned so red Chris asked him how many Warheads he had eaten this time. Jess just walked up the stairs without responding. When he had collected his thoughts enough, he called the only person that he could think of that would know what to do. 

Luke picked up the phone in the diner between yelling at Kirk to decide what kind of bread he wanted and grabbing food from Ceaser to give to Babette. "Luke."  
"Hey, Luke. It's Jess."  
"Jess? What's wrong? Where are you?"  
"Relax, Uncle Luke. I'm fine. I just wanted to ask you something important."  
"Yeah..."  
"Rory just sent me an invitation to her graduation."  
"What?"  
"I know. What does that mean? And what should I do?"  
"Jess, this is big. From what Lorelai told me, Logan wanted to ask Rory to marry him. If Rory is asking you to come to her graduation, that means their relationship is on the fritz, and she needs a rebound. We all know how Rory's rebound turns out for you..."  
Jess was speechless. Perfect blonde dick wanted to marry Rory? Was he insane? Rory had places to go and Rory was independent, not like other girls. In fact, she was like no other girl. Even under the fancy clothes and fancy haircut, she was still Rory, the girl he fell in love with when he was 17 years old. The girl he was still in love with after countless heartbreaks and punches in the gut.

He couldn't go.  
There was no way he could put himself through that heartbreak again. He couldn't do it.

But then why did he want to do it so badly?  
He wanted it bad. He wanted her bad. He wanted 'it' bad. The perfect life that he imagined so many times: Rory in a big house in Philly with two little kids running around him. The boy had a Hemingway book in his hand and the girl had a Rand. He took his son to baseball games and read him him Kerouac books to bed, and let his daughter be a disney princess and listen to the Clash. Rory was a famous overseas correspondent who picked staying at home with him over working and he was a bestselling author with 5 books on the bestselling list and signings all over the country…  
He wanted his dreams.

But there was something holding him back, and he didn't know what it was. He remembered the feeling when Rory had told him that she didn't want to run away with him, and how that moment of utter heartbreak had pushed him through to doing something with his life. He remembered the heartbreak when she told him that the only reason she had come to see Truncheon was to cheat on Dickhead with him to get him back, and how that empowered him to write a full-sized novel and finish college. He remembered that with every hateful, with every hurtful thing Rory Gilmore had ever said to him, he had turned it around to be good.

That was what was holding him back.  
He had to go, because even if she did break his heart once again, he would become a better person because of it.

He liked adversary, he decided. And if what everyone said was true, "absence makes the heart grow stronger," his heart better be a rock.

He laughed; this was going to be an adventure. Who would believe that sullen Jess Mariano was facing his fears head on instead of turning around and running away? He had really grown up.

Huh.


	5. The Best Day

It's done! Hope you like the Lit fluff, this fic has been pretty dismal for major parts of it, so it deserved a happy ending. Thank you for reading, and those who reviewed, I am grateful. Let me know how you like the end.

-socatherine

_Do you hear me,  
I'm talking to you  
Across the water across the deep blue ocean  
Under the open sky, oh my, baby I'm trying_

I'm lucky I'm in love with my best friend  
Lucky to have been where I have been  
Lucky to be coming home again

They don't know how long it takes  
Waiting for a love like this  
Every time we say goodbye  
I wish we had one more kiss  
I'll wait for you I promise you, I will

I'm lucky I'm in love with my best friend  
Lucky to have been where I have been  
Lucky to be coming home again  
Lucky we're in love every way  
Lucky to have stayed where we have stayed  
Lucky to be coming home someday

-Jason Mraz, _Lucky_

Rory breathed in a huge breath of fresh air, and got out of bed, trying not to disturb him. She walked to the kitchen and got herself a cup of coffee that she guessed Matt had already brewed, and made her way to the balcony, her favorite spot in this interesting city. The day was crisp and bright, with no clouds in the sky. She liked this city. It was his home, which automatically made it her home as well.

Funny how things work out.

A year ago, she had sent a desparate invitation to her graduation to Jess. A year ago, her life was in shambles.

Funny how things change.

She smiled, and took a sip of coffee. She liked how, in the early morning, Philly was asleep and all was peaceful, something that reminded her of Stars Hollow. She grabbed the Philedelphia Inquirer she had fetched from the kitchen, and opened to his column.

It had surprised her when he told her that he was writing a biweekly human intrest columnfor the paper on the side of his novels, because he said that it was her that inspired him to open up and write for the masses.

_Second (and third and fourth) Chances _by Jess Mariano, resident silent guy.

"I came to Philedelphia because I was in a bind. Had no money, had no ambition. I was just a pathetic nineteen-year-old kid that picked this stop on the bus because it was the farthest I could come with my fare money.

I stepped off the bus, and lo and behold, and my eyes caught a bookstore. I don't know if it was God or just by chance, but before I knew it, I was in there day in and day out, reading _everything_ I could get my hands on. Everything. Novels, short stories, dictionaries, hell, even poems. And one day, I read something that changed my life, and I basically owe my life to it: Pablo Neruda's poem called _Absense._

_I have scarcely left you  
When you go in me, crystalline,  
Or trembling_

_Or uneasy, wounded by me  
Or overwhelmed with love, as  
when your eyes  
Close upon the gift of life  
That without cease I give you._

My love,  
We have found each other  
Thirsty and we have  
Drunk up all the water and the  
Blood,  
We found each other  
Hungry  
And we bit each other  
As fire bites,  
Leaving wounds in us.

But wait for me,  
Keep for me your sweetness.  
I will give you too  
A rose.

And it reminded me of her. Shit, this poem was _written _about her.

I had spent years trying to forget her. Forget her eyes, forget her smile, forget how beautiful she was when she wasn't wearing make-up, forget her was my kryptonite, my mortal enemy but my one passion in this life all at the same time. In that moment, I knew I had to do _something _with my life, and something that could win her back. So I did.

I wrote _The Subsect_ in a moleskin notebook she gave me. I wrote _Fire's Glory_ after we made love for the first time.

_So let the wind blow us  
To wherever it says  
We are supposed to go  
So let the wind blow us  
To wherever it says  
We are supposed to go_

She is my inspiration. And she is all I need.

(Turn around baby.)"

Rory slowly turned her head, and then gasped. He was on one knee, had bed hair, and holding the most beautiful ring she had ever seen. She automatically compared it to Logan's ring, and giggled. So much better. Everything he did was better. He was mine.

"You're the best thing that has ever happened to me. You're the one I want to wake up to in the morning and you're the one I want to kiss goodnight. You're my best friend. You understand me. You know when I need to be left alone, and you know when I need company. I've wanted to this for so long, but this morning is perfect. Rory Gilmore, will you marry me?"

Rory, crossing her arms, grinned, and said "_What's in store for me in the direction I don't take_?" and lept into his arms.

"_This is the best day of my life, Rory."_ He wispered into her ear, and she couldn't help but kiss him.

So I'm wondering if I should keep writing Jess' column….thoughts anyone? Anywho, thanks for reading, and reviewing.


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